The last few years have not been kind to the reporters of the Los Angeles Times. The top of the masthead has been occupied by four people in the last five years. A newsroom of more than 1,200 people in 2001 now numbers around 600 and further layoffs are ongoing.

Where it came to the institution itself, a rare point of pride among the troops was the company’s handling of sportswriter Mike Penner. In the spring of 2007, just as the Times (and its parent corporation, Tribune Co.) was being sold to real-estate mogul Sam Zell, the veteran columnist announced in an article that he was undergoing hormone therapy and would soon be changing his name to Christine Daniels.

“No amount of surgery is going to turn you into Jennifer Aniston,” says Christina Kahrl, managing editor from Baseball Prospectus who is also transsexual.

The news was shocking to the people who knew Penner and his then-wife Lisa Dillman (who also worked for the paper). But the writer was much beloved throughout the building, and his colleagues at the sports desk—the closest thing a newspaper has to the military, when it comes to frat-like, typically macho guys—turned out to be completely sympathetic and supportive of his decision to have a sex change.

So it came as yet another shock when Daniels resumed life as Mike Penner about a year after the transition, and it came as even more of one when he killed himself around Thanksgiving. Why would a person, whose friends and colleagues were so seemingly supportive, feel so alone about his gender identity that he would decide to commit suicide?

When Penner’s editors first suggested that he write the initial piece announcing his sex change, he was not inclined to do it. But they convinced him it was a good story; it was newsworthy and poignant—and it could be helpful to others, and it was certainly a topic that had been under-explored in the mainstream media. In the end, the decision to write about it was Penner’s, and he agreed.

The response to ”Old Mike, New Christine” was tremendous, providing Penner with a quick emotional lift. Within a day, the article in the Times had received half a million hits online, making it one of the paper’s most popular reads of the year. Some 538 emails arrived in Penner’s old inbox, and all but two of them were supportive.

“He was elated,” says one Times colleague who spoke with Penner in the days following the piece’s publication. “He was really buoyant. Here was this person who was having a renaissance or a metamorphosis and seemed really joyous. It was very positive and moving.”

In a subsequent interview with the paper’s media writer James Rainey, Penner, now Christine Daniels, even admitted, “Writing that piece, which I initially didn’t want to write, ended up becoming one of the best things I’ve ever done.”

What Daniels didn’t know then—what she couldn’t possibly have known, this early in her transition—was just how grueling the hormones can be or what effect being the most prominent American transsexual since tennis player Renée Richards would have on her life.

It’s a problem that at least a few of Penner’s friends and advisers identified. Namely, how does Mike successfully become Christine if she’s stuck permanently with a banner that says “used to be a man”?

One of the first people whom Penner turned to for advice when he decided to begin the process of a sex change was Christina Kahrl, the respected managing editor from Baseball Prospectus who is also transsexual. Kahrl strongly advised Penner to be more cautious about coming out so prominently as a transgender person too early in the process. (Kahrl did not talk publicly about being a transsexual until after completing her transition in 2003 from male to female.) “The transition is difficult enough as is,” she explains. “To make it a public thing in front of millions of people—you could call it crazy or bold or courageous or nuts, and it’s all of those things at once…My advice was not taken.”

Today, Kahrl can understand why the Times is proud of how they handled Penner’s transition (“They made all the appropriate public showings of support and that’s what you hope for from your employer”), but she thinks the initial article—and a blog that followed it, called “Woman in Progress”—were both big mistakes. “It should have been treated as a human-resources matter, not a public-relations opportunity,” she says. “When you put yourself on a stage in front of millions and you’ve been propelled into the role of a celebrity in a community of people that has almost no national celebrities, it’s impossible to go back from it. She or he was permanently 'Christine Daniels-comma-transsexual-sportswriter' or ‘Mike Penner-comma-transsexual-sportswriter.’ You could not turn the clock back from that.”

Meanwhile, Daniels’ private life was thrown into disarray. Her marriage ended. There are indications from friends and colleagues that Daniels had a sexual interest in men. But they also say that she herself wasn’t entirely clear what her romantic life was going to be like or how she planned on navigating it.

“He or she was permanently ‘Mike Penner-comma-transsexual sportswriter.’ You could not turn the clock back.”

“He definitely felt that dating someone of the opposite sex [i.e. being heterosexual as a woman] was part of what was on the landscape,” says Kevin Casey, a former Times photographer and a teammate on an amateur soccer team. “But the bigger thing was trying to get everything together. To me, she seemed more interested in shoes and shopping than all those other details that were yet to be determined.”

So Casey’s parents, who’d known Penner for years, took Christine shopping. At Daniels’ request, Casey took pictures of her for the blog she was doing. “She was pretty persistent. We were trying to help him assimilate into a new lifestyle. That’s when things were pretty fresh and new; things seemed pretty good,” Casey says.

But unquestionably, the transition was more difficult than Christine was letting on. For one, Mike Penner was a person with underlying issues of depression, two former colleagues say. For another, she was going from the strangeness of being a woman who didn't fit in a man’s body to a man who didn’t quite fit in a woman’s.

Mike Penner—49 at the time he began the transition—was over six feet tall, with legs that were big from years of playing soccer. His shoulders were broad, and his neck was large. “He looked OK [as a woman],” says the former colleague. “It wasn’t glaring, you didn’t look and go ‘Oh my God.’ That’s the glass-full version. The glass-half-empty version is that he was a pretty big guy with the build of an athlete. He didn’t have a prominent Adam’s apple that would have been a real obvious identifier, but he wasn’t someone who would easily pass either.”

Passing is a problem many transsexuals face, and it’s an even bigger one for those who make the change later in life, after typically male physical characteristics become more pronounced and after a career exists that makes building a “new” life infinitely more complicated.

“The older you get, the harder it is,” says one male-to-female transsexual, who did not know Mike Penner. “One of the things girls who have made the change will tell you is that you want to do it before the man has time to set in. You see a young girl who’s 21 and she totally looks like a girl, people say ‘she started taking hormones before the man set in.’ It means she was lucky enough to squash the boy before male characteristics set into the body and the hairline starts to look square.”

And even making the transition while still young isn’t foolproof. Says Christina Karhl: “No amount of surgery is going to turn you into Jennifer Aniston.”

Several months into the transition, Daniels dropped out of touch with friends who knew her both as Christine and as Mike.

“She became unresponsive to emails,” Kahrl recalls. “She wasn’t answering calls, whether it was me or other transgender people trying to see how she was doing. We weren’t finding out anything. We were getting nothing.”

Casey, who was living in Seattle, had a similar experience. “I’m not sure what I could have done, short of flying down there and just showing up. And that might have been more destructive than constructive. He pauses: “[My parents and my girlfriend and I] talked about that at one point. We thought, 'Do we hang back or not.'”

In the end, Daniels did not go through with the gender-reassignment surgery and opted to resume life as Mike Penner, a change of heart that’s not so uncommon in transgender cases. (Renée Richards, in her books Second Serve and No Way Renée, discusses at length going on and off hormones before eventually going through with the full sex change operation.)

He apparently convinced his editors at the LA Times to scrub Christine’s blog “Woman in Progress” from the Web site. Doing that was certainly unusual—most news organizations don’t erase things from their Web sites unless they’re found to be seriously inaccurate and/or the subject of a lawsuit—but there was no precedent in the Times’ newsroom for a male-to-female transition, much less one that was being chronicled on the Web, a medium in which the rules of journalism are not yet entirely clear to newspaper companies. Ultimately, the paper was more concerned with Penner’s well-being than his trans-narrative. They complied.

In the office, Penner was not a frequent presence over the next several months of 2009, sources there said, but that’s not so unusual for a sportswriter—even one like Penner who’s no longer primarily on the road covering teams. “Most of those guys work from home,” says a second Times source. This made it easier for Penner to avoid any discussion of the situation, but it also seems to have compounded his tendency toward isolation.

“I think one thing that would be a mistake is to presume that [his suicide] was all about gender,” says a third Times colleague. “Certainly, that was a factor, a big one, but there were other underlying issues and I think one of the mistakes he made was thinking that if this transition takes place, he’d be happy.”

If friends weren’t worried enough to stage some sort of intervention, it’s in part because Penner remained astoundingly productive until just days before his death.

“I don’t recall him missing a day of work,” says one of the former Times colleagues.

“I used the column as a barometer,” says Kevin Casey. “I got the sense that he was keeping busy. Of course that probably means nothing. But they were still there. I thought things were moving along.”

Jacob Bernstein is a senior reporter at The Daily Beast. Previously, he was a features writer at WWD and W Magazine. He has also written for New York magazine, Paper, and The Huffington Post.